


When Derek Met William

by dopeytoad



Category: Check Please! (Webcomic), When Harry Met Sally (1989)
Genre: Alternate Universe, Fluff, M/M
Language: English
Status: In-Progress
Published: 2020-04-17
Updated: 2020-04-17
Packaged: 2021-03-01 02:40:09
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 955
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23187895
Author URL: https://archiveofourown.org/users/dopeytoad/pseuds/dopeytoad
Summary: Derek and William meet when they both drive down to NYC from Samwell, their Alma Mater. Immediately, there a disconnect, and the boys find themselves repeatedly caught in the same routine of back and forth. As the years go by, they keep running into eachother, and their friendship and relationship builds, as they try to keep their friendship untainted by sex.
Relationships: Caitlin Farmer & William "Dex" Poindexter, Chris "Chowder" Chow & Derek "Nursey" Nurse, Denice "Foxtrot" Ford/Shruti (Check Please!), Derek "Nursey" Nurse & William "Dex" Poindexter, Derek "Nursey" Nurse/William "Dex" Poindexter, Justin "Ransom" Oluransi/William "Dex" Poindexter (Brief), Larissa "Lardo" Duan/Derek "Nursey" Nurse (Brief)
Kudos: 5





	When Derek Met William

Will heard him before he saw him. 

He had been waiting in the car for roughly 30 minutes past when Tangredi had arranged for them to meet, which meant that he’d actually been sitting in front of a mangy frat house for roughly 45 minutes, waiting for Tony’s esteemed boyfriend. He only followed about 50 people on instagram; He could only see the same “So Long Samwell!” posts so many damn times. He considered just shifting the car into drive and leaving this frat boy to find his own fucking ride, but Tony had said that bringing him along was dragging along 100% of the gas money, and Will ached to think of the cost the ride would have without Ritchie Riches overflowing pockets.

So he waited. And he scrolled. And he waited. 

He had been caught rereading the long post that his roommate posted when he heard a door open and slam shut, and almost immediately after, a loud yelp of-

“SHIT-” and the clattering of a suitcase on the pavement. Will was almost afraid to look up, and when he did, he was met with easily one of the most attractive people he’d ever seen. 

Sprawled on the grass in front of the steps, Tony’s boyfriend laid there for a few seconds, as though he was used to scenes like this and was taking the time to pause, before he sprung up from the ground, his mouth immediately relaxing into a wide, pearly smile. Will almost wondered if he should get out to help him, worried he hit his head, but by the time he made up his mind to get off his ass, the boy had carried his suitcase and duffle bag towards the car, and his teeth still shined in that bright smile through the window. Will muttered a private litany of swear words, as he stared down the cheerful, wrinkled boy who approached the car. 

Within a few moments of reaching the car door, he tugged on the handle before impatiently knocking on the window, and Will felt irritation flare up in him. This guy had the audacity to be impatient? The redhead huffed, and heavily leaned over the console to tug on the lock, gently opening the door for the boy, dressed in a nice green beanie that complimented his mossy eyes. Will appreciated the rest of his outfit through his irritation, leaning back into his seat as he peeked his head into the car and flashed that confident smile yet again, and Will thought fuck before he realized that the guy was talking. 

“-But I am totally chill with whatever.” He finished, gazing expectantly. Chill, Will’s inner monologue mocked, before he realized that Derek was awaiting an answer to a question he didn’t know.

“Huh?” Will felt bad for a moment, before remembering the reason his ass was numb before he’d even started the roadtrip.

“Trunk or backseat?” Derek asked, “For, uh, the suitcase?” He lifted it up slightly and his lips stretched again and Jesus, Mary, Joseph How much could one kid smile, and was that a chip on the canine-?. This time around, Will folded himself out of the car and opened the trunk before hefting the suitcase and slamming the trunk shut. 

He walked back around to the drivers side and sat himself down, immediately starting the engine, hoping this guy would hurry his ass up and sit the fuck down so they’d get to NYC before they turned 30.

Mr. Green Beanie seemed to exude chill, slowly walking towards the front seat and taking a few moments to gaze at the frat house. He almost looked like he was gonna cry. Will tried not to stare too hard at the obvious broken window and cracked porch, his Uncle Mac probably screaming in pain knowing there was a house in need somewhere.

The boy still stared, so Will slipped a hand onto the horn, and he jumped, before flashing a look at Will that was almost a glare before it melted into indifference. 

Seatbelts, On. GPS, On. Random Guy, Check. Music playing, bingo. Time to roll.

It was barely a minute before Bruce Springsteen found himself cut off by a deep New York accent cutting through the music.

“William Poindexter. Yanno, When Tango described you he never said you were a ginger,” Derek said this as though he were making a scientific observation, rather than picking on the driver's looks. Will’s fingers tightened on the steering wheel. “Name’s Derek, BTW”, except he said “B, T, Dubs” like he was a 16 year old girl with a myspace account.

Gas money. Gas money. Gas money.

“Derek Nurse. Malik Nurse. Derek Malik Nurse” Gas money. “But they just call me Nursey.” Gas money.

“Oh shit, by them I mean, Lol,” Gas money “The team-“

And suddenly a bell rang clear in Will’s head. Team. Hockey. Easy topic. Thank God.

“Ayuh, My team called me Dex back home” Will flicked a look over to Derek, where he basically was lounging, already looking like he belonged in an old italian painting rather than a beat to shit civic.

“Oh no shit, you played hockey?” Derek had pushed himself forwards, and his voice seemed a little more genuine, a little more excited.

“Yeah, D-Man,” Derek opened his mouth to interrupt, a small “M” sound escaping his mouth, but Will kept talking. His irritation from earlier flashed up again, but he continued “I wanted to play in college but I needed to focus on school” And you didn’t get the sports scholarship. 

“Oh totally chill Dexy-“ Gas money. “I majored in English,” Gas money. “It got super stressful with the hockey stuff-“ Gas money.

It was gonna be a long ride.


End file.
